Vacation Home Rentals By Owner In Orleans, MA

Showing 20 Of 255 Vacation Rentals

Exceptional(36)

$804.39

/ Nightly

Private Vacation Home

Your perch to the Cape's best ocean view with private Nauset access for 8!

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(5)

$741.92

/ Nightly

Private Vacation Home

Adorable updated Cape in East Orleans!

Orleans, Massachusetts, United States

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Bath

Sleeps

$747.36

/ Nightly

Private Vacation Home

Sunny, Charming, Farmhouse - Kid Friendly

Orleans, Massachusetts, United States

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Bath

Sleeps

$749.08

/ Nightly

Private Vacation Home

Classic Cape House 5M to Nauset Beach

Orleans, Massachusetts, United States

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Bath

Sleeps

$753.09

/ Nightly

Private Vacation Home

Town Cove Coastal Chic

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(1)

$753.82

/ Nightly

Private Vacation Home

Home to Make Magical Summer Memories

East Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(23)

$758.12

/ Nightly

Private Vacation Home

Peaceful Cape Cod retreat, 1.5mi to National Seashore

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(22)

$772.66

/ Nightly

Private Vacation Home

Steps to Nauset Beach, Private Yard!

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(1)

$774.49

/ Nightly

Private Vacation Home

Capeside: 540-O Vintage Luxury in Orleans

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(62)

$779.98

/ Nightly

Private Vacation Home

10-Minute Walk to Skaket Beach - Orleans - 5 Bikes - Close to Town - 2 AC Units

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(11)

$788.57

/ Nightly

Private Vacation Home

Beach & Golf Hub w/ All-Season Sunroom in Cape Cod

Orleans, Massachusetts, United States

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Bath

Sleeps

$789.05

/ Nightly

Private Vacation Home

Inviting family escape with sunroom, deck, W/D & easy access to Nauset Beach

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$793.2

/ Nightly

Private Vacation Home

Newly Renovated Home

Truro, Massachusetts, United States

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Bath

Sleeps

Exceptional(28)

$800.6

/ Nightly

Private Vacation Home

Five Bedrooms Plus a Fully Equipped Game Room! (2085)

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(8)

$801.87

/ Nightly

Private Vacation Home

4 Minute Walk to Nauset Beach

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(33)

$803.28

/ Nightly

Private Vacation Home

Family Vacation Dream! Firepit, Outdoor Kitchen & Central AC

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(7)

$849.8

/ Nightly

Private Vacation Home

Centrally located Orleans home w/ outdoor seatiing

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(24)

$866.2

/ Nightly

Private Vacation Home

Peaceful Retreat Surrounded by Gardens and Water View

Orleans, Massachusetts, United States

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Bath

Sleeps

$876.12

/ Nightly

Private Vacation Home

Crystal Lake Waterfront Cottage

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(17)

$842.47

/ Nightly

Private Vacation Home

100 Ft to Skaket Beach!

Orleans, Massachusetts, United States

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Bath

Sleeps

Rent a place that suits your needs

Private vacation home

View 255 Private vacation home

Most popular vacation rentals in Orleans

Exceptional(17)

$531.87

/ Nightly

Private vacation home

Experience the charm of Orleans at Skaket Beach Life

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(17)

$579.12

/ Nightly

Private vacation home

3 Mi to Nauset Beach! Family Home w/ Private Yard

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(17)

$578.17

/ Nightly

Private vacation home

Skaket Beach Area Home Sleeps 8

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(17)

$573.31

/ Nightly

Private vacation home

Luxurious, Modern Walk to Water!

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(17)

$571.12

/ Nightly

Private vacation home

Spacious Home Ideally Located a 5 Minute Drive from Nauset Beach

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(17)

$565.29

/ Nightly

Private vacation home

Mid-Century Contemporary

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(17)

$562.23

/ Nightly

Cottage

Captain's Quarters by Nauset Beach

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(17)

$507.78

/ Nightly

Private vacation home

Rock Harbor Retreat: Perfect vacation home: Book Reservations for Summer 2027

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(17)

$499.97

/ Nightly

Private vacation home

Walk to Nauset Beach, Updated and Cozy!

Orleans, Massachusetts, United States

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Bath

Sleeps

Exceptional(17)

$502.34

/ Nightly

Private vacation home

Rock Harbor Hideaway

Orleans, Massachusetts, United States

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Bath

Sleeps

Vacation Home Rentals By Owner In Orleans, MA

$804.39

$741.92

$747.36

$749.08

$753.09

$753.82

$758.12

$772.66

$774.49

$779.98

$788.57

$789.05

$793.2

$800.6

$801.87

$803.28

$849.8

$866.2

$876.12

$842.47

Rent a place that suits your needs

Most popular vacation rentals in Orleans

$531.87

$579.12

$578.17

$573.31

$571.12

$565.29

$562.23

$507.78

$499.97

$502.34

Most Popular Cities in Massachusetts